T3D0167 - 1,2-Diphenylhydrazine
| Record Information | |
|---|---|
| Version | 1.0 |
| Creation Date | 2009-03-06 18:58:12 UTC |
| Update Date | 2013-04-25 08:33:07 UTC |
| Accession Number | T3D0167 |
| Identification | |
| Common Name | 1,2-Diphenylhydrazine |
| Description | 1,2-Diphenylhydrazine is a white solid. It dissolves only slightly in water and does not change into a gas unless it is heated to very high temperatures. It sticks to soil and can be carried into the air along with windblown dust. Once in water or exposed to air it is changed into other chemicals within minutes. These chemicals include the toxic chemicals azobenzene and benzidine. 1,2-Diphenylhydrazine is used to make fabric dyes in other countries, and to make certain medicines. (R761) |
| Compound Type |
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| Chemical Structure |
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| Synonyms |
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| Chemical Formula | C12H12N2 |
| Average Molecular Weight | 184.2371 |
| Monoisotopic Molecular Weight | 184.100048394 |
| Chemical IUPAC Name | hydrazobenzene |
| CAS Registry Number | 122-66-7 |
| SMILES | N(NC1=CC=CC=C1)C1=CC=CC=C1 |
| InChI Identifier | InChI=1S/C12H12N2/c1-3-7-11(8-4-1)13-14-12-9-5-2-6-10-12/h1-10,13-14H |
| InChI Key | InChIKey=YBQZXXMEJHZYMB-UHFFFAOYSA-N |
| Chemical Taxonomy | |
| Kingdom | Organic Compounds |
| Super Class | Benzenoids |
| Class | Benzene and Substituted Derivatives |
| Sub Class | Phenylhydrazines |
| Direct Parent | Phenylhydrazines |
| Alternative Parents |
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| Molecular Framework | Aromatic Homopolycyclic Compounds |
| Substituents |
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| External Descriptors | Not Available |
| External Links | |
| DrugBank ID | Not Available |
| PubChem Compound ID | 31222  |
| KEGG ID | Not Available |
| UniProt ID | Not Available |
| OMIM ID | Not Available |
| ChEBI ID | Not Available |
| BioCyc ID | 4-HYDROXYMETHYLPHENYLHYDRAZINE |
| CTD ID | C032041 |
| Stitch ID | 1,2-Diphenylhydrazine |
| PDB ID | Not Available |
| ACToR ID | 721 |
| Wikipedia Link | Not Available |
| Physical Properties | |
| Appearance | Not Available |
| Melting Point | 131 C |
| Solubility | 0.221 mg/mL at 25 °C [KUHNE,R et al. (1995)] |
| Predicted LogP | 3.763567196666666 |
| Toxicity Profile | |
| Route of Exposure | Not Available |
| Mechanism of Action | Two of the known metabolites, aniline and benzidine, may contribute to the toxicity and/or carcinogenicity of 1,2-diphenylhydrazine. Nonneoplastic liver lesions, hepatocellular carcinomas and/or neoplastic liver nodules indicate that the liver is a target of 1,2-diphenylhydrazine toxicity. As aniline and other aromatic amino metabolites of 1,2-diphenylhydrazine (e.g., aminophenols) are methemoglobinforming compounds by either oral or inhalation routes of exposure, it is possible that 1,2-diphenylhydrazine may cause methemoglobinemia in humans. (R761) |
| Metabolism | Unchanged 1,2-diphenylhydrazine was detected following treatment by all routes, and aniline and benzidine were identified following oral and intraperitoneal treatments. Other metabolites included two unspecified hydroxy derivatives of benzidine (oral route), 2- and 4- aminophenol (intraperitoneal route), and unidentified compounds (oral, intravenous, and intratracheal routes). Aniline is oxidized by hydroxylation of a ring carbon to form 2-or 4-aminophenol or of the nitrogen to form phenylhydroxylamine, and then is conjugated to glucuronic or sulfuric acid. Benzidine is formed readily from 1,2-diphenylhydrazine by acid rearrangement. It has been suggested that benzidine may be produced from 1,2-diphenylhydrazine by acidity in the stomach. (R761) |
| Toxicity Values | LD50: 959 mg/kg (Oral, Rat) (R761) |
| Lethal Dose | Not Available |
| Carcinogenicity (IARC Classification) | Not Available |
| Uses/Sources | 1,2-Diphenylhydrazine is used to make fabric dyes in other countries, and to make certain medicines. Exposure may result from breathing in dust coated with 1,2-diphenylhydrazine and eating dirt or smearing contaminated dirt on the skin. (R761) |
| Minimum Risk Level | Not Available |
| Health Effects | Nonneoplastic liver lesions, hepatocellular carcinomas and/or neoplastic liver nodules; seizures and coma. (R761) |
| Symptoms | Irritatinon to the eyes, nose and respiratory system, depending on the route of exposure. Cough, redness of the exposed surface. (R761) |
| Treatment | Consider gastric lavage after ingestion of a potentially life-threatening amount of poison if it can be performed soon after ingestion. Following inhalation, move patient to fresh air. Monitor for respiratory distress. If cough or difficulty breathing develops, evaluate for respiratory tract irritation, bronchitis, or pneumonitis. Administer oxygen and assist ventilation as required. Treat bronchospasm with inhaled beta2 agonist and oral or parenteral corticosteroids. Irrigate exposed eyes with copious amounts of room temperature water for at least 15 minutes. If the exposure occurs through dermal contact remove contaminated clothing and wash exposed area thoroughly with soap and water. A physician may need to examine the area if irritation or pain persists. (R383) |
| References | |
| General References |
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Targets
1. Estrogen receptor
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Isoform 3 can bind to ERE and inhibit isoform 1.
Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (S301)UniProt ID: P03372
Gene: ESR1
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- S301 — Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors ? and ?: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.
2. Estrogen receptor beta
Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner. Isoform beta-cx lacks ligand binding ability and has no or only very low ere binding activity resulting in the loss of ligand-dependent transactivation ability. DNA-binding by ESR1 and ESR2 is rapidly lost at 37 degrees Celsius in the absence of ligand while in the presence of 17 beta-estradiol and 4-hydroxy-tamoxifen loss in DNA-binding at elevated temperature is more gradual.
Causes endocrine disruption in humans by binding to and inhibiting the estrogen receptor. (S301)UniProt ID: Q92731
Gene: ESR2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report
References:
- S301 — Luft S, Milki E, Glustrom E, Ampiah-Bonney R, O'Hara P. Binding of Organochloride and Pyrethroid Pesticides To Estrogen Receptors ? and ?: A Fluorescence Polarization Assay. Biophysical Journal 2009;96(3):444a.